2-(Hydroxy-meth-yl)pyridinium chloride.

In the title molecular salt, C(6)H(8)NO(+)·Cl(-), the packing is consolidated by N-H⋯Cl and O-H⋯Cl hydrogen bonds, resulting in the formation of [010] chains of alternating cations and anions.

In the title molecular salt, C 6 H 8 NO + ÁCl À , the packing is consolidated by N-HÁ Á ÁCl and O-HÁ Á ÁCl hydrogen bonds, resulting in the formation of [010] chains of alternating cations and anions.

Related literature
The title compound was initially isolated by Boyle et al. (2008). Only the di-substituted pyridine carbonyl HCl salt has been reported previously (Fites et al., 2006).
For support of this research, the authors thank the Office of Basic Energy Science and the US Department of Energy under Contract DE-AC04-94 A L85000. Sandia is a multiprogram laboratory operated by Sandia Corporation, a Lockheed Martin Company, for the United States Department of Energy. Figure 1 shows an atomic displacement ellipsoid plot of 2(hydroxymethyl)pyridinium chloride. The title compound was synthesized through the dissolution of bis(pyridine carbonoxide)titanium(dichloride), (OPy) 2 TiCl 2 , in H 2 O/HCl(5%). The synthesis was optimized by dissolving HOPy in H 2 O/HCl(5%). Fites, et al. (2006) reported the disubstituted salt structure which was isolated from a vanadium 2,6-pyridinedimethanol complex at low pH solutions. This is in agreement to what Boyle et al.(2008) found, where the title compound was isolated from low pH aqueous solutions of the titanium monosubstituted pyridinemethanol complex. Experimental 2(Hydroxymethyl)pyridinium chloride was isolated by Boyle et al.(2008) through the dissolution of a titanium precursor, bis(pyridine carbonoxide)titanium(dichloride) or (OPy) 2 TiCl 2 , (where OPy = pyridine carbonoxide) in acidified water (5% of conc. HCl in water). In order to optimize the synthesis of this salt, crystal were grown via HOPy in acidified water (5% of conc. HCl in water). After slow evaporation, X-ray quality crystals were isolated and characterized by single-crystal X-ray, FTIR, NMR, and EA.

Refinement
H1 (which is bound to O1 of the methanol group) was placed on ideal position, allowed to rotate around the C-O bond and refined via a riding model while H7 was located on difference Fourier maps and allowed to refine freely.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability atomic displacement ellipsoids for non-H atoms. The Cl atom has been translated to clarify interaction with the OH group. Fig. 2. Packing of the title compound on the b-c plane illustrating the NH-Cl-OH intermolecular chain interaction which proceeds parallel to the b axis via the 2 1 screw axis. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.